3514-29-2Relevant articles and documents
Oxymercuration-demercuration of steroidal olefins
Ahmad, M. S.,Raza, S. K.,Kardash, Taufik S.,Ayad, Tariq M.
, p. 855 - 857 (2007/10/02)
Cholest-5-ene (I) on oxymercuration-demercuration affords 5α-cholestan-6β-ol (II) and cholest-4-en-6β-ol (III).Under similar reaction conditions cholest-5-en-3β-yl chloride (IV) gives cholest-5-en-3β-ol (V) and 5α-cholestane-3β,6β-diol (VI).On demercuration with NaBH4-ethylene glycol the mercuriadduct from I gives 6-oxocholest-4-ene (VII), 6-oxocholest-4-en-3β,7α-yl diacetate (VIII), 7-oxocholest-5-en-4α-yl acetate (IX), 6-oxo-cholest-4-en-7α-yl acetate (X) and 7-oxocholest-4-en-3β,6β-diol-3-acetate (XI).Adduct from IV under similar demercuration provides cholest-5-en-3β-yl acetate (XII) and 5α-cholestane-3β,6β-diol diacetate (XIII).Both I and IV failed to provide the expected hydroxy ethers of type XIV in ethylene glycol medium.The identity of these compounds are based on the elemental analyses, spectral data, chemical transformations and comparision with authentic samples where available.
